Winter Park, FL Homes & Real Estate for Sale

Page 2 of 29
569 listings
1872 BISCAYNE DRIVE, Winter Park, FL 32789
Single-Family Home For Sale

$439,000

  • 2 bed |
  • 1 bath |
  • 969 sqft |
1872 BISCAYNE DRIVE Winter Park, FL 32789

#NS1086064 - COLLADO REAL ESTATE

460 CAMBRIDGE BOULEVARD B, Winter Park, FL 32789
Rental Available

$1,850 /mo

  • 2 bed |
  • 2 bath |
  • 945 sqft |
  • 0.35 acre lot
460 CAMBRIDGE BOULEVARD B Winter Park, FL 32789

#O6348824 - 4 ACRE REALTY LLC

1860 VIA CONTESSA, Winter Park, FL 32789
Rental Available

$17,550 /mo

  • 8 bed |
  • 6 bath |
  • 7,000 sqft |
  • 0.26 acre lot
1860 VIA CONTESSA Winter Park, FL 32789

#O6348816 - SIERRA REALTY GROUP LLC

1670 CLEMATIS LANE, Winter Park, FL 32792
Single-Family Home For Sale

$438,900

  • 3 bed |
  • 2 bath |
  • 1,401 sqft |
1670 CLEMATIS LANE Winter Park, FL 32792

#O6348885 - LPT REALTY, LLC

2001 LAKE DRIVE, Winter Park, FL 32789
Single-Family Home For Sale

$2,190,000

  • 5 bed |
  • 4 bath |
  • 4,798 sqft |
  • 0.41 acre lot
2001 LAKE DRIVE Winter Park, FL 32789

#O6336920 - THE AGENCY ORLANDO

600 OLOLU DRIVE, Winter Park, FL 32789
Pending

$2,295,000

  • 4 bed |
  • 4 bath |
  • 3,749 sqft |
  • 0.39 acre lot
600 OLOLU DRIVE Winter Park, FL 32789

#O6348246 - COLDWELL BANKER RESIDENTIAL RE

1530 VIA TUSCANY, Winter Park, FL 32789
Rental Available

$10,500 /mo

  • 4 bed |
  • 4 bath |
  • 3,341 sqft |
  • 0.26 acre lot
1530 VIA TUSCANY Winter Park, FL 32789

#O6348216 - CORCORAN PREMIER REALTY

1500 GAY ROAD 24B, Winter Park, FL 32789
Condominium For Sale

$275,000

  • 2 bed |
  • 2 bath |
  • 1,026 sqft |
1500 GAY ROAD 24B Winter Park, FL 32789

#O6348568 - REALCOM REAL ESTATE SERVICES INC

660 NORTHWOOD CIRCLE, Winter Park, FL 32789
Single-Family Home For Sale

$825,000

  • 4 bed |
  • 3 bath |
  • 2,008 sqft |
660 NORTHWOOD CIRCLE Winter Park, FL 32789

#O6348643 - LUXE HUNTER REAL ESTATE

1900 W FAWSETT ROAD, Winter Park, FL 32789
Single-Family Home For Sale

$3,350,000

  • 4 bed |
  • 5 bath |
  • 4,600 sqft |
  • 1.1 acre lot
1900 W FAWSETT ROAD Winter Park, FL 32789

#O6348512 - KELLER WILLIAMS WINTER PARK

3227 CROWN JEWEL COURT, Orlando, FL 32807
Town Home For Sale

$330,000

  • 3 bed |
  • 3 bath |
  • 1,430 sqft |
3227 CROWN JEWEL COURT Orlando, FL 32807

#TB8432886 - HOME SOLD REALTY LLC

1422 TIERRA CIRCLE, Winter Park, FL 32792
Single-Family Home For Sale

$510,000

  • 4 bed |
  • 2 bath |
  • 1,827 sqft |
1422 TIERRA CIRCLE Winter Park, FL 32792

#O6348045 - CHARLES RUTENBERG REALTY ORLANDO

2004 INDIANA AVENUE, Winter Park, FL 32789
Rental Available

$2,100 /mo

  • 3 bed |
  • 2 bath |
  • 1,340 sqft |
2004 INDIANA AVENUE Winter Park, FL 32789

#S5135674 - KELLER WILLIAMS LEGACY REALTY

1308 S PENNSYLVANIA AVENUE 3, Winter Park, FL 32789
Condominium For Sale

$325,000

  • 1 bed |
  • 1 bath |
  • 823 sqft |
1308 S PENNSYLVANIA AVENUE 3 Winter Park, FL 32789

#O6347787 - EXP REALTY LLC

700 MELROSE AVENUE J 23, Winter Park, FL 32789
Condominium For Sale

$235,000

  • 1 bed |
  • 1 bath |
  • 772 sqft |
  • 871 sqft lot
700 MELROSE AVENUE J 23 Winter Park, FL 32789

#O6347944 - FANNIE HILLMAN & ASSOCIATES

2336 HIGH STREET, Winter Park, FL 32792
Rental Available

$2,375 /mo

  • 4 bed |
  • 2 bath |
  • 1,925 sqft |
2336 HIGH STREET Winter Park, FL 32792

#O6348254 - REAL PROPERTY MANAGEMENT AND REALTY

900 N DENNING DRIVE, Winter Park, FL 32789
Rental Available

$2,495 /mo

  • 4 bed |
  • 3 bath |
  • 1,594 sqft |
900 N DENNING DRIVE Winter Park, FL 32789

#O6348206 - DAHLIA REALTY GROUP

457 E NEW ENGLAND AVENUE, Winter Park, FL 32789
Single-Family Home For Sale

$3,100,000

  • 5 bed |
  • 5 bath |
  • 3,847 sqft |
  • 0.41 acre lot
457 E NEW ENGLAND AVENUE Winter Park, FL 32789

#O6345511 - PREMIER SOTHEBY'S INTL. REALTY

1052 MANCHESTER CIRCLE, Winter Park, FL 32792
Single-Family Home For Sale

$468,500

  • 3 bed |
  • 2 bath |
  • 1,703 sqft |
  • 0.42 acre lot
1052 MANCHESTER CIRCLE Winter Park, FL 32792

#O6347382 - FLORIDA INVESTMENT REALTY GRP

1052 MANCHESTER CIRCLE, Winter Park, FL 32792
Rental Available

$2,650 /mo

  • 3 bed |
  • 2 bath |
  • 1,703 sqft |
  • 0.42 acre lot
1052 MANCHESTER CIRCLE Winter Park, FL 32792

#O6347539 - FLORIDA INVESTMENT REALTY GRP

Presented by - MBA Realty Group, Inc.

Veterans United Homefront
IDX Listings courtesy of Stellar MLS as distributed by MLS GRID.

All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

IDX Copyright 2025 My Florida Regional Multiple Listing Service DBA Stellar MLS. The real estate listing data marked with this icon comes from the IDX program of the Stellar MLS system. All information provided is deemed reliable but is not guaranteed and should be independently verified. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided exclusively for consumers’ personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Properties displayed may be listed or sold by various participants in the MLS. Data displayed may be a portion of, and not a complete set of all listings published in the MLS.

For questions call 1-833-252-8030

Copyright © 2025 MBA Realty Group, Inc. and Did You Serve, LLC. Homefront.com is NOT affiliated with any government agencies, including the VA. Homefront.com is a service of Did You Serve, LLC. Veterans United and the Veterans United House logo are registered trademarks of Mortgage Research Center, LLC, used under license agreement. Terms of Use.